Big Sister helps Little Brother lose his Virginity and teaches him how to please Women

My name is Jessi, let me tell you a little story of how one summer of having my brother live with me became the best summer of my life!!

It all started out a few years ago, I don’t live too far from my mom’s house, about 30 miles. I get to visit every now and then and also get to visit my little brother every now and then. We didn’t have a normal Brother Sister relationship, we didn’t grew up hating each other. In fact it was quite the opposite, we loved each other and were always attached at the hip! We are 7 years apart in age, He had just turned 14 and I had just turned 21.

Dad had died when he was just 2 from a car accident, since then Mom has been with several different men, none lasted. So this year when her new “Boy-Toy” wanted to go on vacation in Europe she jumped at that chance, unfortunately Adam couldn’t go with them. Despite poor Adams cries, he couldn’t stay at his house by himself all that time. At 14 yea he could easily take care of himself to a certain point, but after a while he couldn’t maintain the house, groceries, or anything like that without prior knowledge. So I offered for him to stay at my place for the summer! I had a spare room, well two spare rooms but one room is used for my Massage Business that no one knows about, shit that’s going to be hard to hide from him.

After the phone call from my mom I cursed myself, what the fuck was I thinking? Yea sure I would love to see my brother but several things had to change. Firstly I couldn’t walk around my house naked anymore. I loved being naked, that’s going to suck! Secondly as a college student going to school for Massage Therapy I (illegally) take clients in my home and provide them with a massage for a discounted rate. Its fun I quite enjoy it and it pays the bills. However seeing a different naked man (or sometimes woman) around the house every now and then he wouldn’t get that either. I really didn’t need to do the massages, my bills were covered between my mom helping out, and various grants and school loans, but I loved the extra money it brought in. I never had to ask my mom for a dime beyond what she gives me for rent!

Let me tell you a bit about myself, I’m a very short girl, barefoot I stand 4 foot 11, I’m 21 years old and get mistaken for a 13 year old. My boobs are relatively small too, B cup so I really do look like I’m a Teenager. I don’t mind, I get a lot of attention and I love it! I also have Fiery Red hair and the Freckles to go along with it! My Brother is 14 standing barefoot at 5 foot 0. He is only an Inch taller. Short for a boy his age but the doctors said he hasn’t had his growth yet, but giving that I’m so short, we don’t expect him to get much taller than 5 foot 7.

It was early morning when he was expected in, I was cleaning my massage room and locking it up so he doesn’t discover it when the doorbell rang. Shit, he’s early, and I’m Naked... Fuck fuck fuck. I grabbed the closest thing I could find, my Silk Robe I wore while giving massages. It was very revealing, didn’t cover much, but it was better than being but ass naked in front of my brother and my mom!

“Heyyyyy!!!” I smiled and said as I opened the door to greet my mom and my brother who had headphones on, a backpack, duffle bag and said hi softly while walking in past me. He clearly was not happy
“Come in mom have a coffee, I just woke up” Trying to pass off the reason I had a very revealing robe on
“I can’t sweetie I got to catch my plane soon, Robbie flew off ahead of me to meet a client in Germany and my plane leaves for Rome in an hour, I got to go!”
“Alright Mom have fun, I’ll take care of little squirt here” He hated that name but I liked to flirt with him from time to time!

The First few weeks was relatively Uneventful, I had to stop my clients, and he tried getting in my Massage room more than once. Other than that he pretty much kept to himself. But today I had enough of him sitting in front of my TV Playing his Xbox for every waking moment, and I got tired of sitting around stalking Facebook all day so I decided to do something.

“Hey Kiddo lets go out, hit the beach the mall, maybe a movie” I said to Adam
“Do we have too? I’m about to beat this boss!” I came up and pulled the cord on the Xbox
“Yup we need to have some fun outside! It’s beautiful out here, and we need to spend some time together!”
After several more minutes of arguing he finally agreed and headed to his room to change.
I wanted to hit the beach badly so I put on my favorite Bikini. My favorite Bikini was actually really revealing, Nothing covering my ass as the fabric was small it just hid itself in my ass crack, and there was a very small patch that covered my pussy, as for my top it was just a few strings to hold everything together and some small dots to cover my nipples.
I thought to myself, why do I want this Bikini, I’m going to the beach with my Brother, I need something less revealing! But I put it on anyways, maybe I’ll meet some hot stud! After all I am SUPER Horny right now, I haven’t had sex in Weeks! One of my added benefits to my Massage Business was I had fun while doing it! In truth I would do it for free if I didn’t like money too! The Massages were just too damned fun! Not only did I get the pleasure of being naked while doing it, certain clients I fucked as well. I love sex, can’t get enough of it!

I got fully dressed, I decided on a very skinny string top shirt that left my shoulders, arms, and most of my stomach exposed with a very short shorts to match. Grabbed my purse big enough for my shoes as I enjoy walking around barefoot a lot so I needed a place to hold them as well.

We got to the beach around noon, we played in the water for a few hours, and we had a blast. We would chase each other, try to dunk each other, he even grabbed me a few times and threw me up and then tackled me under water! While doing this he grabbed my ass more than once, I actually quite enjoyed it!

We got out of the water and I wanted to lay out for a while, get a nice tan, and flaunt my amazing body! We both laid side by side enjoying the sun, talking with each other. How’s School, got any friends, Have any Girlfriends? I was really curious on that one. Unfortunately he had told me he had none, never even Kissed a girl, let alone held hands or anything like that. I felt sorry for the kid!

A few Minutes past and a bunch of guys walked past us, all of them were around 15-17 years old, looking at my body they made typical male sexual jokes, and noises thinking that one of them would impress me and I would go home with them. Then they had seen Adam sitting really close to me.

“Hey Nerd, is that your sister over there? Man she’s HOT you should have her come home with me Ill show her a REAL good time “the boy Smiled and pointed to his dick, all the other guys cheered him on and gave him the Guy Ceremonial High Five. Before I even looked at Adam these guys were pissing me off over the sexual comments on me, then I saw Adams face, he was terrified, embarrassed, and he whispered “Those guys go to my school, they bully me all the time, just ignore them they will go away”
“Hey Adams Sister, How would you like a nice long juicy Popsicle to suck on tonight honey!”
That’s it! I had to do something, these guys were Jerks and they were treating my brother like shit. But how did they know we were Brother and Sister, I never went to his school, never met any of his friends, then it hit me, they think I am his sister because he wouldn’t be with such a Hot girl at the beach, let alone with any other girl for that matter
I’m not quite sure what went over me, My desire for human Contact beyond a hug, me being 90% Naked on the beach, or my Anger to these jerks and to help my brother, but I just looked over to them, Smiled, Switched to my right side while looking at them, swung my Left leg over on my brothers legs, moved my bare leg seductively up and down his bare leg, put my arm around his shoulders and held him like he was mine.
“Sorry boys, I’m already spoken for tonight!”
They all laughed, they didn’t believe me
‘Hey Adams Sister, stop trying to stick up for the Geek, we know you would never date some Loser like him!”
Man I wanted to punch these Jerks, but another idea hit me
I leaned over and gave my brother a nice Kiss on the lips, Nothing special, quick peck, then I realized it was just a brother sister kiss
“Ohh look The Geeks sister loves him!” Another Jerk said
“Come here Sister, Let me show you a Real man!”
The Dude cheering continued
What I did next I had no thought over, my horny angry body took over. I reached Over, grabbed my brothers dick then said “I have a REAL Man right here who pleases me every single night for several hours!” then leaned over to give him the best Kiss he has ever had, We locked lips as I started probing my tong to his mouth, instructing it to open, it did right on command, pulsing with each kiss I put my Tong in his mouth, exploring caressing his tong, all while squeezing his now erect dick perfectly on rhythm.
We did this for several minutes, I was actually enjoying it! I had gotten lost in the lust and the wonderful feeling that was my brother I had lost track of time, unfortunately after a few minutes he jerked a few times and I felt my hand start to get wet! Oh shit, He came! I just seriously made my brother cum in his swim trunks, I hope those Jerks didn’t see that or all this would be for nothing!
I got up looked around and they were gone, seemingly surprised Adam had a girlfriend! I can’t believe I gave my brother his first Hand job! Even if it was through his swim trunks, the weird thing was, I enjoyed it, loved it, was not weirded out by it at all, in fact, I wanted MORE.
Adam was a bit embarrassed and wanted to leave the beach right there, I understood but I wanted to stroll the mall for a while, we got dressed and showered up at the shower area at the beach and walked to the Mall.
We strolled the mall for a few hours, I was barefoot the whole time and loved it, I actually was able to convince Adam to join me and he walked without shoes too! It fuled my ever growing excitement! There were a few kids that recognized him and couldn’t believe he had such a hot girlfriend! I held his hand pretty much the whole time and acted like he was my boyfriend. We made out a few more times to make a great show to a few people who still didn’t believe us, and got home a few hours later

“Man Jessi that was a fun day!! Thanks for that, and thanks for the help! I have 5 girls already texting me asking me who you were, a few of them want to hang out next week”

Amazing, I was helping my brother get a girl! IT felt great!
We hung out ate dinner for a bit, but my hunger was not quelled, I was super Horney and I needed to do something about it, Maybe just maybe I can get him to finger me to orgasm, that will do it, I need a good release. After all, I gave him his first hand job today he owes me! But I can’t just ask him, I need a drink!
“Hey Adam” I walked to the living room and sat down next to him, I propped my feet on his lap and he naturally gave them and started rubbing them. Ohhh it felt good
“So you have never kissed a girl before today have you?” I had to ask
“No” he said embarrassingly as he continued an amazing foot rub
“That’s ashamed, you are a GREAT Kisser” He blushed
“Seriously, you are going to make one girl VERY Lucky, Your tong felt amazing! I’m actually quite Jealous! Wish I could give that tong a test on somewhere else” I sarcastically was hinting at my pussy and laughed, He didn’t catch the hint. I moved my foot just slightly to try to feel for his dick, It was there, full staff, I was getting more excited.
“Hey Kiddo, Have you ever had a Massage?”
He looked at me, with a look of curiosity “Nope”
“What? Really? Oh man Massages are GREAT!” I said
“I always wanted one, but I can’t go to a Spa without my mom being there, she would never let me”
I couldn’t hold back anymore, if I can’t have sex at least I can enjoy myself giving a wonderful Massage
“How about now?” I asked already knowing he wanted one
“Now? I don’t have the money for one, and they are closing by now”
I sat up taking my feet out of his wonderful hands, stood in front of him and held out my arms
“Don’t worry kiddo, I have a secret, and you can’t tell mom!”
“Ok” he said grabbing my hands as I helped pull him up
I led him to my secret room, his hand in mine. I was excited like a Kid showing his mom his favorite candy store. I put the key in and Unlocked the room, opened the door and flipped the switch.
Dim lighting turned on along with a low volume calm CD that I had playing, my massage room came to life
“What’s this” he asked
“It’s a Professional Massage room, I give Massages to people in here on my off time, and I really enjoy it!”
“Wow, so you are going to give me a massage?”
“Yup Kiddo! That’s right, now get naked!”
“Naked?” he was shocked, but looked excited at the same time. I could clearly see his buldge in his Gym shorts. He wanted this!
“That’s right silly, I can’t give you a massage with cloths on”
“Burt you have cloths on….” He was stunned, He couldn’t believe he said that, neither could I, but what shocked me more was what I said next
“I do, Fine, we are in this together, you take off a piece of clothing and so will I. If you are getting a massage Naked it’s only fair I perform it Just as Naked.
He didn’t say anything, just looked at me with shock and awe in his face, then he nodded and slowly went to grab his shirt, making sure I was going to hold up my end of the bargen. I saw this and I did the same, grabbing the bottom of my tank top I had on and started to lift it over my head. In a few seconds we were both Topless, I didn’t have a bra on so my Boobs were exposed, I did nothing to try to cover them up.
My Shirtless Brother was just starting at them, in amazement.
“Have you ever seen a woman’s Boobs before?”
“Only in Porn” he said
Ohhh he watches porn!! I like!
“Do you want to touch them?”
I didn’t have to ask twice, he came closer and cupped both my boobs and lightly caressed them, it was making me super excited
After a few moments I told him to stop and to get a move on with this so he can get a massage, he understood backed up a bit and began unbuttoning his shorts.
I did the same, we dropped the at the same time. We were both standing there, he was completely naked, didn’t wear any Underwear. I however had a thong on, barefoot of course.
“This isn’t fair” he said as I was just staring at his erect dick, it wasn’t big but it was a decent size for a 14 year old boy!
“What?” I said out of my daze, he pointed at my thong “Oh” I replied as I took it off.
We were both standing there completely Naked, I was really enjoying myself, and clearly he was too. I gave him a quick tease, and show of my whole body before saying “Ok lay down face down on the table”
He laid down as I gathered my Oils and Lubricants.
For about an Hour I caressed every part of his back, running my hands up and down his back, touched and caressed his hands and his feet, he really enjoyed that, and for my enjoyment I got up, straddled his back, and rubbed my naked body all over his back. That felt great! But it was not enough, my pussy was on fire! I was hoping he would rub it while I gave him the massage but he didn’t.
“Alright Kiddo” I said getting off his back
“Awww, does it have to end already? It felt sooo good. I LOVED your body on me!” He thinks it’s over? I laughed
“No Adam, It’s not over you silly goose! Turn Over” I said
“Wa-What?”
“I have to do your front, so turnover”
He slowly and reluctantly turned over as he had no idea why he was supposed to, embarrassed by his erect penis he covered it up with his hands
I grabbed his hands and put them by his side as I wanted to stare at it
“Silly you, don’t be embarrassed, Your naked, I’m naked, you are getting a very Intimate experience, it’s only Natural to be excited” I said trying to ease him
“Are…Are you?” he asked
“Yea silly, of course I am, I have a hot naked guy in front of me who I am touching every part of his body while being naked myself, and Of course I am excited!” At this point I couldn’t control myself. I continued to oil his front up, then began caressing his chest, moving to his arms, hands, neck, legs and feet. All the while lightly brushing his dick but never touching it.
“Hey Sis” he said “can we kiss again like we did on the beach?” he just blurted out.
“If you really want too, sure that would be fun!” I said while massaging his feet.
I got done with his feet, walked up to his front, started caressing his chest, bent down and we made out again, this time his tong was probing inside my mouth. We made out for a few minutes, while I tried to massage his chest, failing a few times I came down to his dick, and brushed it a bit. I stopped the kissed and asked,
“Have you ever had a proper Hand job before?”
“This morning was the first” he said
“Want one?”
He just nodded as I grabbed his shaft for the first time, this time my bare hand was on his bare shaft and I could tell him LOVED IT. His head bucked back and his eyes closed, his pelvis thrusted upward a bit. I wrapped my hand around it and stroked his shaft a few times before I could tell he was getting a bit close. No not yet, I still had a lot I wanted to do with him!
I stopped my attention to his dick and he looked up at me
“Please don’t stop, that felt amazing”
“I won’t, but you are about to get your first Blow job!”
He looked at me with excited eyes as I wrapped my mouth over his cock, locked my lips and sucked in, slowly taking it out, making that pop noise, replacing my lips and licking his shaft up and down with my Tong. His head went back again as he was in pure bliss!! I bobbed my head a few more times than felt his hips buck up, he grabbed my head, then shot his load in my mouth! IT tasted WONDERFUL!
I kept his cum in my mouth, savoring its flavor and waiting for it to be done, as he was done I took his cock out of my mouth, stuck my tong out to show him his seed, and then swallowed every drop!
“Oh my god Jessi that was amazing!”
“Oh I’m not done yet!” I said
I climbed up and straddled him, leaned down putting my body to his, slid up and down, making every inch of my naked body slide on a part of his. I eventually met his face and saw his lips, I grabbed both his hands in mine and we made out again. This time we made out for a solid 5 minutes, oh he tasted so delicious! After a while I felt his dick get hard again and it was pushing on my belly, while not missing a beat with our tong battle we had, I moved my legs wide, pushed up and rested my pussy on his dick, then started giving his dick a wonderful pussy massage without penetrating. After a few moments of this I broke the kiss and looked right into his eyes.
“Adam, do you want to go further?” I asked
All he did was nod, I sat up, got up a little, grabbed his dick, positioned it right below my pussy and slowly sat down on it. Inch by Inch I slowly pushed it inside of me as I sat down, Oh my god it felt GREAT!
Adam was caressing my body the whole time I was slowly sliding over his wonderful cock, eventually I hit bottom then started rocking back and forth. Oh man it felt great, his dick rocking around inside of me, while he caressed my boobs. I was close to coming, I changed paces a bit, put my feet on the table, bent my knees, then started pumping up and down, faster and faster, and his dick was sliding in and out of me at a very quick pace. I was so Horney I kept screaming louder and Louder, eventually I felt his hips buck, he started moaning loud and I felt his dick Explode in me, That was enough for me to SLAM down on his dick as hard as I could, and my whole body went Limp, Shaking very violently and I came in a very Intense orgasm.
Our Collective Cum puddled around us, I laid on top of him his dick still inside of me, I loved this feeling, We laid there for hours, seemingly sleeping the night away. I was in his arms, he was inside of me. My legs wrapped around his pelvis, never wanting him to leave my protection, never wanting his dick out of me. We passed out until the morning still in this position. I woke up feeling his dick hard in me, put him back on his back, and started again, riding his cock in and out of me waking him up from his sleep, and Cumming a few minutes later again and again. We never got dressed that day, instead we fucked everywhere. The Couch, kitchen Table, my bed. Actually we never got dressed for a week straight, but we just fucked. His 14 year old Youth showed amazing Stamina!